US6320081B1 - O-Nitro(thio)phenol derivatives, and their preparation - Google Patents
O-Nitro(thio)phenol derivatives, and their preparation Download PDFInfo
- Publication number
- US6320081B1 US6320081B1 US09/161,149 US16114998A US6320081B1 US 6320081 B1 US6320081 B1 US 6320081B1 US 16114998 A US16114998 A US 16114998A US 6320081 B1 US6320081 B1 US 6320081B1
- Authority
- US
- United States
- Prior art keywords
- nitro
- nitrophenol
- compound
- preparation
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 0 *#[3H]c1ccccc1C.*#[3H]c1ccccc1C.C#[C-]C.C#[C-]C.C#[C-]C.CC.C[3H]C.Cc1ccccc1[N+](=O)[O-] Chemical compound *#[3H]c1ccccc1C.*#[3H]c1ccccc1C.C#[C-]C.C#[C-]C.C#[C-]C.CC.C[3H]C.Cc1ccccc1[N+](=O)[O-] 0.000 description 12
- YABIWWWKTYIXSD-UHFFFAOYSA-N Cc1c(O)c(F)c(Oc2ccc([N+](=O)[O-])c(OCc3ccccc3)c2)c(F)c1F Chemical compound Cc1c(O)c(F)c(Oc2ccc([N+](=O)[O-])c(OCc3ccccc3)c2)c(F)c1F YABIWWWKTYIXSD-UHFFFAOYSA-N 0.000 description 2
- ODMKDBZWWJLVIK-UHFFFAOYSA-N O=[N+]([O-])c1ccc(O)cc1OCc1ccccc1 Chemical compound O=[N+]([O-])c1ccc(O)cc1OCc1ccccc1 ODMKDBZWWJLVIK-UHFFFAOYSA-N 0.000 description 2
- MCLNBWMSVILJDJ-IRNTWATGSA-N C#[3H]C.C#[3H]c1ccccc1C.C#[C-]C Chemical compound C#[3H]C.C#[3H]c1ccccc1C.C#[C-]C MCLNBWMSVILJDJ-IRNTWATGSA-N 0.000 description 1
- BKKKSHUJFOBVKX-UHFFFAOYSA-N C=CCOc1c(C)c(F)c(F)c(C)c1F Chemical compound C=CCOc1c(C)c(F)c(F)c(C)c1F BKKKSHUJFOBVKX-UHFFFAOYSA-N 0.000 description 1
- ZBDJHTOKWKFJSE-UHFFFAOYSA-N C=CCOc1c(C)c(F)c(F)c(O)c1F Chemical compound C=CCOc1c(C)c(F)c(F)c(O)c1F ZBDJHTOKWKFJSE-UHFFFAOYSA-N 0.000 description 1
- RDBLEDATXOUQTK-UHFFFAOYSA-N C=CCOc1c(C)c(F)c(F)c(OCc2ccccc2)c1F Chemical compound C=CCOc1c(C)c(F)c(F)c(OCc2ccccc2)c1F RDBLEDATXOUQTK-UHFFFAOYSA-N 0.000 description 1
- FIGMPCMCBNNOBY-UHFFFAOYSA-N C=CCOc1c(C)c(F)c(F)c(Oc2c(F)c(F)c([N+](=O)[O-])c(F)c2F)c1F Chemical compound C=CCOc1c(C)c(F)c(F)c(Oc2c(F)c(F)c([N+](=O)[O-])c(F)c2F)c1F FIGMPCMCBNNOBY-UHFFFAOYSA-N 0.000 description 1
- DLYZPNNVAGUOJV-UHFFFAOYSA-N C=CCOc1c(C)c(F)c(F)c(Oc2c(F)c(O)c(C)c(F)c2F)c1F Chemical compound C=CCOc1c(C)c(F)c(F)c(Oc2c(F)c(O)c(C)c(F)c2F)c1F DLYZPNNVAGUOJV-UHFFFAOYSA-N 0.000 description 1
- UHOJYCYIBZHOFI-UHFFFAOYSA-N C=CCOc1c(C)c(F)c(F)c(Oc2c(F)c(O)c([N+](=O)[O-])c(F)c2F)c1F Chemical compound C=CCOc1c(C)c(F)c(F)c(Oc2c(F)c(O)c([N+](=O)[O-])c(F)c2F)c1F UHOJYCYIBZHOFI-UHFFFAOYSA-N 0.000 description 1
- IZIBFQYBWAOPNV-UHFFFAOYSA-N Cc1c(F)c(F)c(OCc2ccccc2)c(F)c1F Chemical compound Cc1c(F)c(F)c(OCc2ccccc2)c(F)c1F IZIBFQYBWAOPNV-UHFFFAOYSA-N 0.000 description 1
- RJEUXYDPWHSKQH-UHFFFAOYSA-N Cc1c(F)c(F)c(Oc2ccc([N+](=O)[O-])c(OCc3ccccc3)c2)c(F)c1F Chemical compound Cc1c(F)c(F)c(Oc2ccc([N+](=O)[O-])c(OCc3ccccc3)c2)c(F)c1F RJEUXYDPWHSKQH-UHFFFAOYSA-N 0.000 description 1
- OIRNZWNINCQOIY-UHFFFAOYSA-N Cc1ccc(Oc2ccc([N+](=O)[O-])c(O)c2)cc1OCc1ccccc1.Cc1ccccc1 Chemical compound Cc1ccc(Oc2ccc([N+](=O)[O-])c(O)c2)cc1OCc1ccccc1.Cc1ccccc1 OIRNZWNINCQOIY-UHFFFAOYSA-N 0.000 description 1
- WIGRWFZJYYVRMX-UHFFFAOYSA-N Cc1ccc(Oc2ccc([N+](=O)[O-])c(OCc3ccccc3)c2)cc1OCc1ccccc1 Chemical compound Cc1ccc(Oc2ccc([N+](=O)[O-])c(OCc3ccccc3)c2)cc1OCc1ccccc1 WIGRWFZJYYVRMX-UHFFFAOYSA-N 0.000 description 1
- HLWRJWMRVGUUPM-UHFFFAOYSA-N Nc(c(O)c(c(O)c1F)F)c1F Chemical compound Nc(c(O)c(c(O)c1F)F)c1F HLWRJWMRVGUUPM-UHFFFAOYSA-N 0.000 description 1
- WHOVFYLXXIZGNP-UHFFFAOYSA-N Nc1c(O)c(F)c(Oc2c(F)c(O)c(N)c(F)c2F)c(F)c1F Chemical compound Nc1c(O)c(F)c(Oc2c(F)c(O)c(N)c(F)c2F)c(F)c1F WHOVFYLXXIZGNP-UHFFFAOYSA-N 0.000 description 1
- OVSPDVXJRZRCNZ-UHFFFAOYSA-N Nc1ccc(Oc2c(F)c(O)c(N)c(F)c2F)cc1O Chemical compound Nc1ccc(Oc2c(F)c(O)c(N)c(F)c2F)cc1O OVSPDVXJRZRCNZ-UHFFFAOYSA-N 0.000 description 1
- FFXSDAGPJYALFE-UHFFFAOYSA-N Nc1ccc(Oc2ccc(N)c(O)c2)cc1O Chemical compound Nc1ccc(Oc2ccc(N)c(O)c2)cc1O FFXSDAGPJYALFE-UHFFFAOYSA-N 0.000 description 1
- FOYQTDKPDAJMPF-UHFFFAOYSA-N O=[N+]([O-])c1ccc(F)cc1OCc1ccccc1 Chemical compound O=[N+]([O-])c1ccc(F)cc1OCc1ccccc1 FOYQTDKPDAJMPF-UHFFFAOYSA-N 0.000 description 1
- AVYHOLJLPHZEHA-UHFFFAOYSA-M O=[N+]([O-])c1ccc(O[K])cc1OCc1ccccc1 Chemical compound O=[N+]([O-])c1ccc(O[K])cc1OCc1ccccc1 AVYHOLJLPHZEHA-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Definitions
- the invention relates to novel o-nitrophenol derivatives and o-nitrothiophenol derivatives, which are also jointly abbreviated to o-nitro(thio)phenol derivatives, and to a process for their preparation.
- Bis-o-nitrophenols can be prepared by nitrating bisphenols. However, this gives isomers and also polynitro compounds, which is very disadvantageous since, if the nitration is not complete, i.e. to 100%, and does not take place entirely isomer-free, i.e. nitration only taking place in the o-position to the hydroxyl group, then the reduction is in some cases followed by the formation of aminophenols which do not allow complete cyclization in the PBO precursor and considerably impair the properties of the polybenzoxazole.
- nitrophenol derivatives i.e. bis(o-benzyloxynitrophenyl) compounds
- This is achieved by nucleophilic substitution (see “Polymer Preprints”, in loco citato).
- this process requires high temperatures, namely significantly higher temperatures than 100° C. (solutions in dimethylacetamide/toluene are refluxed).
- high reaction temperatures promote side-reactions, which reduce the yield (it is a maximum of 73%) and make purification of the target product more difficult.
- the bis-o-aminophenols prepared in this way are not stable to oxidation.
- the object of the invention is to provide o-nitrophenol derivatives and o-nitrothiophenol derivatives which are suitable for the preparation of selected o-aminophenols or o-aminothiophenols of high isomer purity and stability to oxidation which serve as particularly suitable monomers for the preparation of polymer precursors.
- a 1 A 3 are—independently of one another—H, F, CH 3 , CF 3 , OCH 3 , OCF 3 , CH 2 CH 3 , CF 2 CF 3 , OCH 2 CH 3 or OCF 2 CF 3 ;
- R alkyl, alkoxyalkyl, alkenyl, alkoxyalkenyl, alkynyl or alkoxyalkynyl, each having a maximum of 6 carbon atoms, phenyl, phenacyl or benzyl, and benzylalkyl, benzylalkenyl, benzyloxyalkyl, benzyloxyalkenyl, benzylalkoxyalkyl or benzylalkoxyalkenyl, each having a maximum of four aliphatic carbon atoms;
- R* H or R
- R in the o-nitro(thio)phenol derivative (1), R cannot be alkyl if A 1 is an F-atom in the m-position to the NO 2 group, A 2 and A3 are H, and the TH group is in the o-position to the NO 2 group.
- the characterization “A 1 -A 3 ” in the structural formulae means that the nitrophenyl groups contain radicals A 1 , A 2 and A 3 .
- the corresponding radicals in the two nitrophenyl groups may be identical or different.
- the o-amino(thio)phenols which can be prepared from the o-nitro(thio)phenol derivatives of the invention result in polymer precursors which, after cyclization, give polybenzoxazoles or polybenzothiazoles which have low moisture absorption, high temperature stability and a high degree of planarization.
- the polymer precursors are readily soluble in many organic solvents, such as acetone, cyclohexanone, ethyl lactate, diethylene glycol mono- and diethyl ether, N-methylpyrrolidone and ⁇ -butyrolactone, and in aqueous-alkaline developers containing no metal ions.
- the precursors can easily be applied to substrates, such as silicon wafers, by spin-coating methods, they form uniform films, and can readily be cyclized on the substrate.
- the o-nitro(thio)phenol derivatives of the formula (1) can be prepared by selectively removing the radical R 2 from a compound of the structure
- the nitro compound of the structure shown above can be prepared from the corresponding dihalogen compound (X in place of R 1 T and R 2 T) by reaction with compounds R 1 TH and R 2 TH, for example allyl alcohol and benzyl alcohol, or with corresponding alkali metal salts.
- o-nitro(thio)phenol derivatives of structure (1) can be prepared by reacting a compound of the structure
- R 1 and R 2 preferably have the following meanings: methyl, ethyl, isopropyl, allyl or methoxymethyl, and phenyl, phenacyl (i.e. C 6 H 5 —CO—CH 2 —), benzyl or benzyloxymethyl.
- the metals employed for the selective removal of R 2 are preferably Ni, Se, Rh, Pd, Pt and Hg, and the metal compounds can be salts, organometallic compounds or complex compounds, such as (CH 3 COO) 2 Pd(C 6 H 5 ) 3 .
- the removal is advantageously carried out using Pd/C (palladium/carbon), SeO 2 or HgCl.
- the basic agent acts as a source of the anion TH ⁇ and can be an alkali metal hydroxide, carbonate, or hydrogen carbonate; an alkaline earth metal hydroxide; an aqueous solution of a tertiary or quaternary nitrogen base, such as tetramethylammonium hydroxide; or an aqueous solution of an alkali hydrogen sulfide, such as sodium hydrogen sulfide.
- the reactions are generally carried out in a solvent.
- suitable solvents are dimethylformamide, dimethylacetamide, dimethyl sulfoxide, N-methyl-pyrrolidone and ⁇ -butyrolactone.
- the o-nitro(thio)phenol derivatives are obtained in a yield of ⁇ 85%.
- o-nitro(thio)phenol derivatives of the invention are also suitable for the preparation of o-amino(thio)phenolcarboxylic acids, which are likewise used for the preparation of polybenzoxazoles and polybenzothiazoles or the corresponding polymer precursors.
- the preparation of o-amino-(thio)phenolcarboxylic acids is described in the simultaneously filed German Patent Application No. 197 42 194.6—“o-Amino(thio)phenolcarboxylic acids, and their preparation” (GR 97 P 3689).
- the mixture is then allowed to cool to room temperature, and the reaction product is filtered off via a Büuchner funnel and rinsed three times with a mixture of tetrahydrofuran and petrol ether (volume ratio 1:1).
- the reaction product is then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
- reaction product crystallizes from the initially viscous solution.
- the precipitated reaction product is then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
- the organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator.
- the precipitated reaction product is then recrystallized from a mixture of n-hexane and methylene chloride (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
- the organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator.
- the precipitated crude product is then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
- reaction solution is then filtered via a fluted filter, and the crude product is extracted by shaking with 200 ml of ethyl acetate and 400 ml of water.
- the organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator.
- the precipitated reaction product is then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
- the yellow solution is evaporated to half in a rotary evaporator and left to stand at room temperature overnight, during which the reaction product precipitates in crystalline form.
- the reaction product is then separated off and dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
- the organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator.
- the precipitated reaction product is then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Characterization: |
Mass spectrum: | molecular peak at 232 | ||
Elemental analysis: | |||
Theoretical value (in %): | C: 62.1 H: 5.2 N: 12.1 | ||
Found (in %): | C: 61.8 H: 5.4 N: 12.1 | ||
m.p.: | 209° C. | ||
Characterization: |
Mass spectrum: | molecular peak at 442 | ||
Elemental analysis: | |||
Theoretical value (in %): | C: 40.7 H: 1.1 N: 6.3 | ||
Found (in %): | C: 40.7 H: 1.0 N: 6.3 | ||
Characterization: |
Mass spectrum: | molecular peak at 440 | ||
Elemental analysis: | |||
Theoretical value (in %): | C: 40.9 H: 1.4 N: 6.4 | ||
Found (in %): | C: 40.9 H: 1.4 N: 6.3 | ||
Claims (13)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742135 | 1997-09-24 | ||
DE19742135 | 1997-09-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
US6320081B1 true US6320081B1 (en) | 2001-11-20 |
Family
ID=7843469
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/161,149 Expired - Lifetime US6320081B1 (en) | 1997-09-24 | 1998-09-24 | O-Nitro(thio)phenol derivatives, and their preparation |
Country Status (4)
Country | Link |
---|---|
US (1) | US6320081B1 (en) |
EP (1) | EP0905121B1 (en) |
JP (1) | JPH11171841A (en) |
DE (1) | DE59804641D1 (en) |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2385282A (en) | 1942-09-23 | 1945-09-18 | Lyneh And Company | 2-nitro-3-methoxy-phenol and process of making same |
DE1178440B (en) | 1962-11-17 | 1964-09-24 | Bayer Ag | Process for the preparation of 3-alkoxy-4-nitrophenols |
US3350459A (en) | 1962-11-16 | 1967-10-31 | Bayer Ag | Mercapto-nitrophenols and a process for preparing them |
US3947434A (en) | 1973-06-06 | 1976-03-30 | Morton-Norwich Products, Inc. | 9-(P-phenylazoanilino)-7-methyl-1H-imidazo[4,5-f]quinolines |
US4310527A (en) | 1976-01-08 | 1982-01-12 | Ciba-Geigy Corporation | Etherified hydroxy quinazolone compounds |
US4419122A (en) * | 1981-10-19 | 1983-12-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-3'-oxygen-substituted-4'-substituted diphenyl ethers |
SU1205518A1 (en) | 1983-10-24 | 1986-09-30 | Отделение Нефтехимии Института Физико-Органической Химии И Углехимии Ан Усср | Bis(3-amino-4-oxyphenoxy)perfluorarylenes as monomers for producing polybenzoxazoles with higher thermal and hydrolytic stability |
EP0264678A1 (en) | 1986-10-02 | 1988-04-27 | Hoechst Celanese Corporation | Polyamides with hexafluoroisopropylidene groups, positively acting photosensitive compositions, and recording materials using them |
EP0300326A1 (en) | 1987-07-21 | 1989-01-25 | Hoechst Celanese Corporation | Hydroxypolyimides and high temperature resistant positive photoresists |
EP0317942A2 (en) | 1987-11-24 | 1989-05-31 | Hoechst Celanese Corporation | Heat resistant polyamides and polybenzoxazoles from bis-[(aminohydroxyphenyl hexafluoro-isopropyl] diphenyl ethers |
US5503640A (en) | 1988-03-03 | 1996-04-02 | L'oreal | 3-substituted para-aminophenols, process for preparing them, their use for dyeing keratinous fibres and the intermediate compounds used in the preparation process |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919238A (en) * | 1973-06-06 | 1975-11-11 | Morton Norwich Products Inc | 9-(Substituted amino)imidazo(4,5-f) quinolines |
ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
-
1998
- 1998-09-12 DE DE59804641T patent/DE59804641D1/en not_active Expired - Lifetime
- 1998-09-12 EP EP98117330A patent/EP0905121B1/en not_active Expired - Lifetime
- 1998-09-24 JP JP10270394A patent/JPH11171841A/en active Pending
- 1998-09-24 US US09/161,149 patent/US6320081B1/en not_active Expired - Lifetime
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2385282A (en) | 1942-09-23 | 1945-09-18 | Lyneh And Company | 2-nitro-3-methoxy-phenol and process of making same |
US3350459A (en) | 1962-11-16 | 1967-10-31 | Bayer Ag | Mercapto-nitrophenols and a process for preparing them |
DE1178440B (en) | 1962-11-17 | 1964-09-24 | Bayer Ag | Process for the preparation of 3-alkoxy-4-nitrophenols |
US3947434A (en) | 1973-06-06 | 1976-03-30 | Morton-Norwich Products, Inc. | 9-(P-phenylazoanilino)-7-methyl-1H-imidazo[4,5-f]quinolines |
US4310527A (en) | 1976-01-08 | 1982-01-12 | Ciba-Geigy Corporation | Etherified hydroxy quinazolone compounds |
US4419122A (en) * | 1981-10-19 | 1983-12-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-3'-oxygen-substituted-4'-substituted diphenyl ethers |
SU1205518A1 (en) | 1983-10-24 | 1986-09-30 | Отделение Нефтехимии Института Физико-Органической Химии И Углехимии Ан Усср | Bis(3-amino-4-oxyphenoxy)perfluorarylenes as monomers for producing polybenzoxazoles with higher thermal and hydrolytic stability |
EP0264678A1 (en) | 1986-10-02 | 1988-04-27 | Hoechst Celanese Corporation | Polyamides with hexafluoroisopropylidene groups, positively acting photosensitive compositions, and recording materials using them |
EP0300326A1 (en) | 1987-07-21 | 1989-01-25 | Hoechst Celanese Corporation | Hydroxypolyimides and high temperature resistant positive photoresists |
EP0317942A2 (en) | 1987-11-24 | 1989-05-31 | Hoechst Celanese Corporation | Heat resistant polyamides and polybenzoxazoles from bis-[(aminohydroxyphenyl hexafluoro-isopropyl] diphenyl ethers |
US5503640A (en) | 1988-03-03 | 1996-04-02 | L'oreal | 3-substituted para-aminophenols, process for preparing them, their use for dyeing keratinous fibres and the intermediate compounds used in the preparation process |
Non-Patent Citations (12)
Title |
---|
CA:116:209649 abs of Toxicol Environ Chem by Brodskii E, 34 (2-4) pp 105-112, 1992.* |
CA:123:169595 abs of JP06293640, Feb. 1994.* |
CA:129:275910 abs of WO 9842680, Oct. 1998.* |
CA:74:111715 abs Of J Chem Soc C (3) pp 562-566, 1971.* |
CA:87:189338 abs of Planta Med By Glombitza 32(1) pp 33-45, 1977.* |
CA:92:181056 abs of Khim. Geterotsikl. Soedin. (12) pp 1620-1623 by Korshak, 1979. * |
CA:95:220393 abs of Acta Polym 32 (8) by Mikitaev pp 435-460, 1981.* |
CA:99:175374 abs of EP83204, Jul. 1983.* |
Chemical Abstracts No. XP-002087377, vol. 72 (1970), May 25 No. 21, p. 399. |
International Application WO 97/23216 (Bigge et al.), dated Jul. 3, 1997. |
Journal of Med. Chem. vol. 8 by Augstein pp 446-454, 1965.* |
Jules Freedman et al.: "The Preparation of 3,4-Dihydro-1-benzoxepin-5(2H)-ones", J. Heterocyclic Chem., 26, 1547 (1989), pp. 1547-1553. |
Also Published As
Publication number | Publication date |
---|---|
EP0905121B1 (en) | 2002-07-03 |
JPH11171841A (en) | 1999-06-29 |
DE59804641D1 (en) | 2002-08-08 |
EP0905121A1 (en) | 1999-03-31 |
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